I had a long phone call with a CEO of a company on Friday. He’s had an intense few weeks and was clearly stressed out. His summary was “my stomach hurts.” My objective view of his business is that it’s fine – lots of things are going well – but there are plenty of issues he needs to address and they don’t necessarily have a short term time horizon for resolution.

This reminded me of a question I received from another friend a few months ago:

I thought of you yesterday as I was speaking with a new business acquaintance. She was telling me about all her new business ventures, including a talk show concept. She has already made a connection with an industry source who is helping her fine tune and sell it. As I congratulated her on the progress she’s made, she said, “This is so new to me. I try to listen to my gut instincts, but the fear gets in the way.” Assuming that your entrepreneurs (particularly first-time entrepreneurs) are aware of at least some of the risks involved with starting any company, do you ever have to advise them how to manage their fear so it doesn’t get in the way of their potential success?

I have long believed that fear, anxiety, and guilt are useless emotions in an entrepreneurial context. When I get into an existential discussion with some people about this, they argue that there are contexts where these are useful emotions, but I still haven’t found them. So – my first advice is “let go of the fear and anxiety (and guilt) – immediately.”

In my first company I was an anxious entrepreneur. I felt the full burden of the business and even though I had a great business partner, I internalized all the ups and downs of the business. I pushed through the anxiety regularly, which I imagine impacted my current style (which I like to think of as intense/playful) – much of which was forged from my experience with my first company and some of my big successes and failures from the 1998 – 2002 time frame.

“Letting go of fear and anxiety” isn’t trivial – nor is it automatic – but it can be done. During my Friday afternoon CEO conversation, my friend acknowledged that he wasn’t panicked, but he felt close. It was clear he was physically and mentally exhausted from the effort he was putting into his company.

When I’m tired, things go to hell. My first indicator is that when something good happens I feel happy and when something bad happens I feel unhappy. I used to just accept this as part of my reality – now I know this means I need a break. Sometimes it’s just a weekend; other times it’s a week.

“Fear is the mindkiller” is my favorite quote from Dune (one of the all time greatest sci-fi books.) Fear – at least for me in an entrepreneurial context – almost always comes from fatigue. It’s really difficult to rationally address the issues that cause you fear when you are tired – which just makes the cycle more difficult.

I told my friend to take the weekend off. He should turn off his computer, don’t try to “catch up on email”, don’t try to “fix anything, let the thoughts about his business roll through his head, but spend time with himself and his wife. And sleep. As much as he wanted to (I got up at 10:24am this morning.) On Monday, he should come back refreshed, not anxious, and ready to address the issues that he’s facing.